Hydrogen Bonding and the ortho Effect in Acetonitrile. Reaction of ortho-Substituted Benzoic Acids with Amines

1965 ◽  
Vol 87 (12) ◽  
pp. 2534-2539 ◽  
Author(s):  
J. F. Coetzee ◽  
G. P. Cunningham
Keyword(s):  
Hydrogen Bonding ◽  
Benzoic Acids ◽  
Ortho Effect ◽  
Substituted Benzoic Acids

Molecular Cocrystals of Carboxylic Acids. XXVI Adducts of the Amino-Substituted Benzoic Acids with Nitroaromatic Lewis Bases: the Influence of Associative Polyfunctional Substituents on Self-Assembly of Molecules in Cocrystallization Processes

1997 ◽  
Vol 50 (10) ◽  
pp. 977 ◽  
Author(s):  
Daniel E. Lynch ◽  
Graham Smith ◽  
Karl A. Byriel ◽  
Colin H. L. Kennard
Keyword(s):  
Hydrogen Bonding ◽  
Infrared Spectroscopy ◽  
Self Assembly ◽  
Benzoic Acids ◽  
Aminobenzoic Acid ◽  
X Ray Diffraction ◽  
X Ray ◽  
Lewis Bases ◽  
Aminobenzoic Acids ◽  
Substituted Benzoic Acids

A series of molecular adducts of the isomeric aminobenzoic acids with the nitro-substituted Lewis bases 2-chloro-5-nitropyridine, 5-nitroquinoline and 5-nitroisoquinoline has been prepared and characterized by using infrared spectroscopy and X-ray powder diffraction, and in four cases by single-crystal X-ray diffraction methods. These four compounds are the adducts of 3-aminobenzoic acid with 5-nitroquinoline [(C7H7NO2)(C9H6N2O2)], 4-aminobenzoic acid with 5-nitroquinoline [(C7H7NO2)2(C9H6N2O2)], 2-aminobenzoic acid with 5-nitroisoquinoline [(C7H7NO2)(C9H6N2O2)] and 4-aminobenzoic acid with 5-nitroisoquinoline [(C7H7N2O2)(C9H6N2O2)]. Other compounds described are the (1 : 1) adducts of 4-aminobenzoic acid with 2-chloro-5-nitropyridine, and 2-aminobenzoic acid with 5-nitroquinoline. All adducts involve hydrogen-bonding network associations while in none of the examples is any proton transfer involved.

THE STUDY OF HYDROGEN BONDING AND RELATED PHENOMENA BY ULTRAVIOLET LIGHT ABSORPTION: PART III. THE STRENGTH OF THE DIMERIC HYDROGEN BOND IN SUBSTITUTED BENZOIC ACIDS AS A MEASURE OF ELECTRONIC AND STERIC INTERACTIONS

1960 ◽  
Vol 38 (5) ◽  
pp. 728-735 ◽  
Author(s):  
W. F. Forbes ◽  
A. R. Knight ◽  
D. L. Coffen
Keyword(s):  
Hydrogen Bond ◽  
Hydrogen Bonding ◽  
Concentration Dependence ◽  
Intramolecular Hydrogen Bond ◽  
Light Absorption ◽  
Benzoic Acids ◽  
Steric Interactions ◽  
Substituted Benzoic Acids ◽  
Intramolecular Hydrogen ◽  
Methoxybenzoic Acid

The strength of the intermolecular (dimeric) hydrogen bond in substituted benzoic acids, as estimated from the observed concentration dependence of the ultraviolet absorption spectra, is found to vary with the nature and the position of the substituent. The effects of a number of substituents on the strength of the dimeric hydrogen bond can be rationalized in terms of the usual electronic and steric interactions. The data indicate that o-methoxybenzoic acid forms a stronger intramolecular hydrogen bond than o-fluorobenzoic acid.

Analysis of the ortho effect: acidity of 2-substituted benzoic acids

2004 ◽  
Vol 28 (1) ◽  
pp. 67-74 ◽  
Author(s):  
Stanislav Böhm ◽  
Pavel Fiedler ◽  
Otto Exner
Keyword(s):  
Benzoic Acids ◽  
Ortho Effect ◽  
Substituted Benzoic Acids

THE BASICITIES OF ORTHO-SUBSTITUTED BENZOIC ACIDS

1961 ◽  
Vol 39 (12) ◽  
pp. 2508-2515 ◽  
Author(s):  
Ross Stewart ◽  
Maurice R. Granger
Keyword(s):  
Hydrogen Bonding ◽  
Benzoic Acid ◽  
Sulphuric Acid ◽  
Benzoic Acids ◽  
Methyl Ethyl ◽  
Alkyl Groups ◽  
Substituted Benzoic Acids

The basicities of 15 ortho-substituted benzoic acids have been measured in sulphuric acid. The ortho effects of alkyl groups are base weakening and increase in the expected order methyl, ethyl, i-propyl, t-butyl. Ortho halo benzoic acids have comparable basicities and are weaker than their para isomers. Oxygen-containing ortho substituents, except hydroxyl, all cause substantial base strengthening relative to the para isomers. Even the groups nitro and carboxyl when substituted ortho in benzoic acid cause the basicity to rise, presumably because of hydrogen bonding in the conjugate acids.

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